JPS6230197B2 - - Google Patents
Info
- Publication number
- JPS6230197B2 JPS6230197B2 JP53107492A JP10749278A JPS6230197B2 JP S6230197 B2 JPS6230197 B2 JP S6230197B2 JP 53107492 A JP53107492 A JP 53107492A JP 10749278 A JP10749278 A JP 10749278A JP S6230197 B2 JPS6230197 B2 JP S6230197B2
- Authority
- JP
- Japan
- Prior art keywords
- methanol
- ethyl acetate
- substance
- absorption spectrum
- chloroform
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 72
- 239000000126 substance Substances 0.000 claims description 35
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 15
- 238000000862 absorption spectrum Methods 0.000 claims description 12
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 claims description 11
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 7
- 239000000741 silica gel Substances 0.000 claims description 7
- 229910002027 silica gel Inorganic materials 0.000 claims description 7
- 238000004809 thin layer chromatography Methods 0.000 claims description 7
- 230000003115 biocidal effect Effects 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 5
- 238000000921 elemental analysis Methods 0.000 claims description 5
- 238000002844 melting Methods 0.000 claims description 5
- 230000008018 melting Effects 0.000 claims description 5
- 239000002246 antineoplastic agent Substances 0.000 claims description 4
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 claims description 4
- 239000003242 anti bacterial agent Substances 0.000 claims 2
- 229940088710 antibiotic agent Drugs 0.000 claims 2
- GATAXMKQDPALOM-QYPOQKIVSA-N antibiotic sf-1739 Chemical compound OC1=C(C)C(=O)C(=O)C([C@H]2CO)=C1[C@@H]1N3CCO[C@H]3[C@@H]3C[C@H]4N(C)[C@@H]3[C@@H]1N2[C@@H]4O GATAXMKQDPALOM-QYPOQKIVSA-N 0.000 claims 1
- 229940041181 antineoplastic drug Drugs 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 7
- 230000009102 absorption Effects 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- 230000001093 anti-cancer Effects 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 206010028980 Neoplasm Diseases 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 4
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- 241000187747 Streptomyces Species 0.000 description 2
- 230000007059 acute toxicity Effects 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
- -1 alkaline earth metal salts Chemical class 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 239000003518 caustics Substances 0.000 description 2
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- ZRXHLJNBNWVNIM-UHFFFAOYSA-N 3-methyl-1-benzofuran Chemical compound C1=CC=C2C(C)=COC2=C1 ZRXHLJNBNWVNIM-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000192125 Firmicutes Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- ICAIHGOJRDCMHE-UHFFFAOYSA-O ammonium cyanide Chemical compound [NH4+].N#[C-] ICAIHGOJRDCMHE-UHFFFAOYSA-O 0.000 description 1
- 230000002022 anti-cellular effect Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- GESRUPNWDGSYQI-UHFFFAOYSA-N bromylformonitrile Chemical compound O=Br(=O)C#N GESRUPNWDGSYQI-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000012084 conversion product Substances 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000003022 immunostimulating agent Substances 0.000 description 1
- 230000003308 immunostimulating effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- FKWSMBAMOQCVPV-UHFFFAOYSA-N magnesium dicyanide Chemical compound [Mg+2].N#[C-].N#[C-] FKWSMBAMOQCVPV-UHFFFAOYSA-N 0.000 description 1
- 239000000401 methanolic extract Substances 0.000 description 1
- XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229940127084 other anti-cancer agent Drugs 0.000 description 1
- 229940047091 other immunostimulants in atc Drugs 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
Landscapes
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Compounds Of Unknown Constitution (AREA)
Priority Applications (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10749278A JPS5535009A (en) | 1978-09-04 | 1978-09-04 | New antibiotic sf-1739hp-c and hp-f, their preparation and anticarcinogen having new antibiotic sf-1739hp-c and hp-f as active component |
| GB7903605A GB2017079B (en) | 1978-02-08 | 1979-02-01 | Substance sf-1739 derivatives |
| US06/008,406 US4209509A (en) | 1978-02-08 | 1979-02-01 | Substance SF-1739 derivatives, process for preparing the same and antibacterial compositions containing the same |
| DE2904628A DE2904628C2 (de) | 1978-02-08 | 1979-02-07 | Substanz SF-1739 HP-C, Verfahren zu deren Herstellung und Mittel mit antibakterieller und Antitumor-Wirkung, welche diese Substanz enthalten |
| FR7903149A FR2416899A1 (fr) | 1978-02-08 | 1979-02-07 | Derives de la substance sf-1739, leur preparation et leurs utilisations therapeutiques |
| DE2954282A DE2954282C2 (de) | 1978-02-08 | 1979-02-07 | Substanz SF-1739 HP, Verfahren zu deren Herstellung und Mittel mit antibakterieller und Antitumor-Wirkung, welche diese Substanz enthalten |
| NLAANVRAGE7904766,A NL186514C (nl) | 1978-08-16 | 1979-06-19 | Derivaten van de verbinding sf-1739, werkwijzen voor de bereiding daarvan en antibacteriele en antitumor preparaten, die deze verbindingen bevatten. |
| SE7905693A SE445921B (sv) | 1978-08-16 | 1979-06-28 | Derivat av substansen sf-1739, benemnd sf-1739 hp-c, framstelld genom odling av streptomyces griseoplanus stam sf-1739(atcc 31451) och komposition innehallande substansen |
| CH606479A CH642667A5 (en) | 1978-08-16 | 1979-06-28 | Derivatives of the substance SF-1739, process for the preparation of such derivatives and antibacterial and cancer-preventing preparations containing such derivatives |
| IT24026/79A IT1121986B (it) | 1978-08-16 | 1979-06-29 | Composti ad azione antibatterica e antitumorale,procedimento per fabbricarli e composizioni che li contengono |
| ES482569A ES8301500A1 (es) | 1978-08-16 | 1979-06-29 | Procedimiento para la fabricacion de antibioticos complejos antitumorales y antibacterianos. |
| CA330,894A CA1105450A (en) | 1978-08-16 | 1979-06-29 | Substance sf-1739 derivatives, process for preparing the same and antibacterial and antitumor compositions containing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10749278A JPS5535009A (en) | 1978-09-04 | 1978-09-04 | New antibiotic sf-1739hp-c and hp-f, their preparation and anticarcinogen having new antibiotic sf-1739hp-c and hp-f as active component |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5535009A JPS5535009A (en) | 1980-03-11 |
| JPS6230197B2 true JPS6230197B2 (enrdf_load_html_response) | 1987-07-01 |
Family
ID=14460572
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10749278A Granted JPS5535009A (en) | 1978-02-08 | 1978-09-04 | New antibiotic sf-1739hp-c and hp-f, their preparation and anticarcinogen having new antibiotic sf-1739hp-c and hp-f as active component |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5535009A (enrdf_load_html_response) |
-
1978
- 1978-09-04 JP JP10749278A patent/JPS5535009A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5535009A (en) | 1980-03-11 |
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